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Mesoionic 1,2,4‐triazolo[4,3‐ c ]quinazolines
Author(s) -
Gineinah Magdy M.,
Ismaiel Abd ElKader M.,
ElKerdawy Mohamed M.,
Glen Richard A.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270346
Subject(s) - mesoionic , chemistry , quinazoline , phosgene , ring (chemistry) , free base , stereochemistry , combinatorial chemistry , medicinal chemistry , salt (chemistry) , organic chemistry
Because of the close structural similarity between triazoloquinazolines and certain 5‐membered ring mesoionic heterocycles, all of which possess antiinflammatory activity, we prepared several examples of the novel mesoionic 1,2,4‐triazolo[4,3‐ c ]quinazoline ring system for their therapeutic potential. These compounds can be prepared by the cyclization of the appropriately substituted 4‐hydrazinoquinazolines with phosgene. When the mesoionic product was unsubstituted at the 5‐position ( i.e. , quinazoline 2‐position), it could only be isolated as its hydrochloride salt and not as its unstable free base. None of the mesoionic products were sufficiently stable in solution to allow for evaluation of their antiinflammatory activity.